NPASS Compound

Structure

NPC141817 OpenBabel07101719512D 26 28 0 0 1 0 0 0 0 0999 V2000 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 17 1 0 0 0 0 8 13 2 0 0 0 0 8 19 1 0 0 0 0 9 15 2 0 0 0 0 9 16 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 1 1 6 0 0 0 11 12 1 0 0 0 0 11 20 1 0 0 0 0 12 2 1 1 0 0 0 12 21 1 0 0 0 0 14 15 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 18 2 0 0 0 0 16 22 1 0 0 0 0 17 19 2 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 13 1 1 0 0 0 21 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.16
Volume:	371.599
LogP:	3.312
LogD:	3.302
LogS:	-4.71
# Rotatable Bonds:	4
TPSA:	64.99
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.896
Synthetic Accessibility Score:	3.368
Fsp3:	0.381
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.749
MDCK Permeability:	2.5827035642578267e-05
Pgp-inhibitor:	0.866
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.778

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	97.33892059326172%
Volume Distribution (VD):	0.746
Pgp-substrate:	2.8406317234039307%

ADMET: Metabolism

CYP1A2-inhibitor:	0.27
CYP1A2-substrate:	0.968
CYP2C19-inhibitor:	0.779
CYP2C19-substrate:	0.906
CYP2C9-inhibitor:	0.839
CYP2C9-substrate:	0.834
CYP2D6-inhibitor:	0.282
CYP2D6-substrate:	0.896
CYP3A4-inhibitor:	0.902
CYP3A4-substrate:	0.876

ADMET: Excretion

Clearance (CL):	8.882
Half-life (T1/2):	0.435

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.185
Drug-inuced Liver Injury (DILI):	0.859
AMES Toxicity:	0.224
Rat Oral Acute Toxicity:	0.206
Maximum Recommended Daily Dose:	0.613
Skin Sensitization:	0.062
Carcinogencity:	0.061
Eye Corrosion:	0.003
Eye Irritation:	0.106
Respiratory Toxicity:	0.906

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC141817

Natural Product ID:	NPC141817
*Common Name:**	Arisantetralone D
IUPAC Name:	(2R,3S,4R)-4-(3,4-dimethoxyphenyl)-7-hydroxy-6-methoxy-2,3-dimethyl-3,4-dihydro-2H-naphthalen-1-one
Synonyms:	Arisantetralone D
Standard InCHIKey:	DRKPZVVNEGETTG-FKANQGBASA-N
Standard InCHI:	InChI=1S/C21H24O5/c1-11-12(2)21(23)15-9-16(22)18(25-4)10-14(15)20(11)13-6-7-17(24-3)19(8-13)26-5/h6-12,20,22H,1-5H3/t11-,12-,20-/m1/s1
SMILES:	C[C@@H]1[C@@H](C)C(=O)c2cc(c(cc2[C@H]1c1ccc(c(c1)OC)OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1080598
PubChem CID:	14078176
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003425] Aryltetralin lignans

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19673515]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[20536188]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[23265871]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT927	Cell Line	PBMC	Homo sapiens	Inhibition	=	34.1	%	PMID[505541]
NPT927	Cell Line	PBMC	Homo sapiens	Inhibition	=	70.1	%	PMID[505541]
NPT927	Cell Line	PBMC	Homo sapiens	Inhibition	=	83.9	%	PMID[505541]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC141817 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	1530
0.2-0.3	3408
0.3-0.4	9024
0.4-0.5	9418
0.5-0.6	3175
0.6-0.7	7347
0.7-0.8	7515
0.8-0.85	749
0.85-0.9	125
0.9-0.95	32
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC229218
1.0	High Similarity	NPC192597
1.0	High Similarity	NPC169214
1.0	High Similarity	NPC176030
0.9481	High Similarity	NPC95485
0.9481	High Similarity	NPC88065
0.9481	High Similarity	NPC89504
0.9362	High Similarity	NPC160777
0.9362	High Similarity	NPC73416
0.9291	High Similarity	NPC309169
0.9291	High Similarity	NPC196941
0.9231	High Similarity	NPC52692
0.9178	High Similarity	NPC164912
0.9172	High Similarity	NPC58310
0.9172	High Similarity	NPC295977
0.9155	High Similarity	NPC91694
0.9155	High Similarity	NPC300603
0.9143	High Similarity	NPC78987
0.9143	High Similarity	NPC82336
0.9111	High Similarity	NPC66905
0.911	High Similarity	NPC302783
0.911	High Similarity	NPC78505
0.911	High Similarity	NPC118427
0.911	High Similarity	NPC306011
0.911	High Similarity	NPC144283
0.911	High Similarity	NPC473201
0.911	High Similarity	NPC472838
0.9103	High Similarity	NPC237441
0.9085	High Similarity	NPC46161
0.9085	High Similarity	NPC46880
0.9085	High Similarity	NPC239608
0.9028	High Similarity	NPC39361
0.9014	High Similarity	NPC125134
0.9014	High Similarity	NPC86455
0.9014	High Similarity	NPC137920
0.8993	High Similarity	NPC213401
0.8973	High Similarity	NPC261322
0.8966	High Similarity	NPC58373
0.8951	High Similarity	NPC50954
0.8944	High Similarity	NPC84273
0.8936	High Similarity	NPC223336
0.8919	High Similarity	NPC312338
0.8919	High Similarity	NPC149889
0.8897	High Similarity	NPC304622
0.8889	High Similarity	NPC32163
0.8889	High Similarity	NPC123228
0.8889	High Similarity	NPC151167
0.8889	High Similarity	NPC16651
0.8889	High Similarity	NPC5018
0.8889	High Similarity	NPC123722
0.8889	High Similarity	NPC276466
0.8881	High Similarity	NPC11314
0.8873	High Similarity	NPC28398
0.8873	High Similarity	NPC29599
0.8859	High Similarity	NPC305710
0.8851	High Similarity	NPC124842
0.8828	High Similarity	NPC225351
0.8824	High Similarity	NPC234175
0.8819	High Similarity	NPC209085
0.8819	High Similarity	NPC224884
0.8815	High Similarity	NPC90128
0.8815	High Similarity	NPC276014
0.8815	High Similarity	NPC303680
0.8815	High Similarity	NPC179777
0.8815	High Similarity	NPC84076
0.8808	High Similarity	NPC199463
0.8808	High Similarity	NPC178976
0.8808	High Similarity	NPC37543
0.8786	High Similarity	NPC252343
0.8784	High Similarity	NPC475718
0.8777	High Similarity	NPC327410
0.8776	High Similarity	NPC474903
0.8759	High Similarity	NPC207732
0.8742	High Similarity	NPC14561
0.8742	High Similarity	NPC77807
0.8742	High Similarity	NPC279605
0.8742	High Similarity	NPC288353
0.8742	High Similarity	NPC5379
0.8741	High Similarity	NPC257589
0.8741	High Similarity	NPC228771
0.8741	High Similarity	NPC266705
0.8741	High Similarity	NPC53305
0.8741	High Similarity	NPC29008
0.8733	High Similarity	NPC62051
0.8725	High Similarity	NPC272566
0.8725	High Similarity	NPC75377
0.8716	High Similarity	NPC37220
0.8716	High Similarity	NPC472837
0.8707	High Similarity	NPC77598
0.8705	High Similarity	NPC50763
0.8705	High Similarity	NPC239302
0.8701	High Similarity	NPC149389
0.8699	High Similarity	NPC157133
0.8684	High Similarity	NPC296044
0.8684	High Similarity	NPC167098
0.8681	High Similarity	NPC472410
0.8676	High Similarity	NPC92207
0.8676	High Similarity	NPC127937
0.8676	High Similarity	NPC177925
0.8667	High Similarity	NPC3744
0.8667	High Similarity	NPC137125
0.8667	High Similarity	NPC30216
0.8658	High Similarity	NPC472279
0.8649	High Similarity	NPC474556
0.8636	High Similarity	NPC311740
0.863	High Similarity	NPC105213
0.863	High Similarity	NPC275278
0.863	High Similarity	NPC472836
0.8627	High Similarity	NPC245891
0.8627	High Similarity	NPC104876
0.8621	High Similarity	NPC312256
0.8609	High Similarity	NPC107109
0.8603	High Similarity	NPC9067
0.8601	High Similarity	NPC284409
0.8601	High Similarity	NPC470962
0.86	High Similarity	NPC70320
0.86	High Similarity	NPC267091
0.8593	High Similarity	NPC474691
0.8593	High Similarity	NPC257976
0.8593	High Similarity	NPC4181
0.8593	High Similarity	NPC242372
0.8593	High Similarity	NPC164778
0.8592	High Similarity	NPC324929
0.8592	High Similarity	NPC90431
0.859	High Similarity	NPC26386
0.8582	High Similarity	NPC144662
0.8571	High Similarity	NPC84571
0.8571	High Similarity	NPC478019
0.8561	High Similarity	NPC172673
0.8552	High Similarity	NPC110419
0.8551	High Similarity	NPC307050
0.8551	High Similarity	NPC277458
0.8551	High Similarity	NPC226661
0.8543	High Similarity	NPC131121
0.8542	High Similarity	NPC474784
0.8535	High Similarity	NPC263212
0.8533	High Similarity	NPC225854
0.8533	High Similarity	NPC243891
0.8533	High Similarity	NPC85131
0.8531	High Similarity	NPC264022
0.8529	High Similarity	NPC273686
0.8529	High Similarity	NPC312404
0.8523	High Similarity	NPC55327
0.8521	High Similarity	NPC153088
0.8521	High Similarity	NPC139519
0.8521	High Similarity	NPC204592
0.8519	High Similarity	NPC114298
0.8516	High Similarity	NPC472906
0.8514	High Similarity	NPC165389
0.8514	High Similarity	NPC58752
0.8511	High Similarity	NPC111845
0.8511	High Similarity	NPC294226
0.8503	High Similarity	NPC142165
0.8497	Intermediate Similarity	NPC470762
0.8497	Intermediate Similarity	NPC474167
0.8487	Intermediate Similarity	NPC475770
0.8487	Intermediate Similarity	NPC93552
0.8487	Intermediate Similarity	NPC25127
0.8487	Intermediate Similarity	NPC472905
0.8487	Intermediate Similarity	NPC474000
0.8483	Intermediate Similarity	NPC326065
0.8483	Intermediate Similarity	NPC470035
0.8478	Intermediate Similarity	NPC203719
0.8478	Intermediate Similarity	NPC117237
0.8477	Intermediate Similarity	NPC256406
0.8472	Intermediate Similarity	NPC469680
0.8472	Intermediate Similarity	NPC469681
0.8472	Intermediate Similarity	NPC471974
0.8467	Intermediate Similarity	NPC264550
0.8467	Intermediate Similarity	NPC333691
0.8467	Intermediate Similarity	NPC69430
0.8467	Intermediate Similarity	NPC142876
0.8467	Intermediate Similarity	NPC134293
0.8467	Intermediate Similarity	NPC195763
0.8467	Intermediate Similarity	NPC200060
0.8467	Intermediate Similarity	NPC264289
0.8467	Intermediate Similarity	NPC139293
0.8467	Intermediate Similarity	NPC40290
0.8462	Intermediate Similarity	NPC7464
0.8456	Intermediate Similarity	NPC470757
0.8456	Intermediate Similarity	NPC106659
0.8456	Intermediate Similarity	NPC229084
0.8456	Intermediate Similarity	NPC163083
0.8456	Intermediate Similarity	NPC160900
0.8456	Intermediate Similarity	NPC18984
0.8452	Intermediate Similarity	NPC161947
0.8452	Intermediate Similarity	NPC155302
0.8452	Intermediate Similarity	NPC185617
0.8451	Intermediate Similarity	NPC176814
0.8451	Intermediate Similarity	NPC5310
0.8451	Intermediate Similarity	NPC300776
0.8451	Intermediate Similarity	NPC4982
0.8451	Intermediate Similarity	NPC68779
0.8446	Intermediate Similarity	NPC287495
0.8446	Intermediate Similarity	NPC9370
0.8446	Intermediate Similarity	NPC75295
0.8446	Intermediate Similarity	NPC30890
0.8444	Intermediate Similarity	NPC201777
0.8442	Intermediate Similarity	NPC143328
0.8442	Intermediate Similarity	NPC129684

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC141817 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	951
0.2-0.3	1348
0.3-0.4	2462
0.4-0.5	2124
0.5-0.6	1103
0.6-0.7	658
0.7-0.8	163
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8478	Intermediate Similarity	NPD9494	Approved
0.8456	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD7473	Discontinued
0.8228	Intermediate Similarity	NPD6232	Discontinued
0.8129	Intermediate Similarity	NPD2801	Approved
0.8065	Intermediate Similarity	NPD1934	Approved
0.8054	Intermediate Similarity	NPD8166	Discontinued
0.8025	Intermediate Similarity	NPD3882	Suspended
0.8013	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7458	Discontinued
0.7986	Intermediate Similarity	NPD3972	Approved
0.7941	Intermediate Similarity	NPD5536	Phase 2
0.7933	Intermediate Similarity	NPD4628	Phase 3
0.7933	Intermediate Similarity	NPD7003	Approved
0.7931	Intermediate Similarity	NPD3620	Phase 2
0.7931	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD1283	Approved
0.7872	Intermediate Similarity	NPD1876	Approved
0.7866	Intermediate Similarity	NPD5844	Phase 1
0.7857	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD5977	Approved
0.7848	Intermediate Similarity	NPD5978	Approved
0.7826	Intermediate Similarity	NPD1651	Approved
0.7824	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD6234	Discontinued
0.7792	Intermediate Similarity	NPD6273	Approved
0.7791	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6166	Phase 2
0.7791	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2935	Discontinued
0.7785	Intermediate Similarity	NPD1465	Phase 2
0.7778	Intermediate Similarity	NPD5283	Phase 1
0.7778	Intermediate Similarity	NPD1511	Approved
0.7748	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD2346	Discontinued
0.7727	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD37	Approved
0.7718	Intermediate Similarity	NPD2799	Discontinued
0.7707	Intermediate Similarity	NPD7028	Phase 2
0.7697	Intermediate Similarity	NPD3818	Discontinued
0.7692	Intermediate Similarity	NPD1470	Approved
0.7687	Intermediate Similarity	NPD943	Approved
0.7677	Intermediate Similarity	NPD1512	Approved
0.7671	Intermediate Similarity	NPD3764	Approved
0.766	Intermediate Similarity	NPD1281	Approved
0.7654	Intermediate Similarity	NPD5494	Approved
0.7643	Intermediate Similarity	NPD3226	Approved
0.7643	Intermediate Similarity	NPD3019	Approved
0.7639	Intermediate Similarity	NPD2798	Approved
0.7633	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD228	Approved
0.7616	Intermediate Similarity	NPD2344	Approved
0.76	Intermediate Similarity	NPD1510	Phase 2
0.76	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD4380	Phase 2
0.7584	Intermediate Similarity	NPD1607	Approved
0.7578	Intermediate Similarity	NPD4966	Approved
0.7578	Intermediate Similarity	NPD4967	Phase 2
0.7578	Intermediate Similarity	NPD4965	Approved
0.7568	Intermediate Similarity	NPD1240	Approved
0.7568	Intermediate Similarity	NPD4060	Phase 1
0.7562	Intermediate Similarity	NPD7819	Suspended
0.7535	Intermediate Similarity	NPD1201	Approved
0.7532	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6190	Approved
0.7518	Intermediate Similarity	NPD2932	Approved
0.7517	Intermediate Similarity	NPD230	Phase 1
0.7516	Intermediate Similarity	NPD3817	Phase 2
0.7515	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7074	Phase 3
0.7485	Intermediate Similarity	NPD7228	Approved
0.7483	Intermediate Similarity	NPD3027	Phase 3
0.7481	Intermediate Similarity	NPD3022	Approved
0.7481	Intermediate Similarity	NPD3021	Approved
0.7468	Intermediate Similarity	NPD3750	Approved
0.7468	Intermediate Similarity	NPD4110	Phase 3
0.7468	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD2979	Phase 3
0.744	Intermediate Similarity	NPD7054	Approved
0.7438	Intermediate Similarity	NPD6873	Phase 2
0.7434	Intermediate Similarity	NPD2438	Suspended
0.7431	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7075	Discontinued
0.7421	Intermediate Similarity	NPD824	Approved
0.7419	Intermediate Similarity	NPD2309	Approved
0.7407	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD447	Suspended
0.7396	Intermediate Similarity	NPD7472	Approved
0.7394	Intermediate Similarity	NPD7199	Phase 2
0.7394	Intermediate Similarity	NPD6959	Discontinued
0.7394	Intermediate Similarity	NPD4626	Approved
0.7394	Intermediate Similarity	NPD8127	Discontinued
0.7389	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1471	Phase 3
0.7383	Intermediate Similarity	NPD8032	Phase 2
0.7368	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7095	Approved
0.7361	Intermediate Similarity	NPD1608	Approved
0.7346	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1549	Phase 2
0.7329	Intermediate Similarity	NPD6386	Approved
0.7329	Intermediate Similarity	NPD6385	Approved
0.7315	Intermediate Similarity	NPD6798	Discontinued
0.7315	Intermediate Similarity	NPD3268	Approved
0.7315	Intermediate Similarity	NPD2313	Discontinued
0.7312	Intermediate Similarity	NPD3455	Phase 2
0.7308	Intermediate Similarity	NPD2354	Approved
0.7305	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6355	Discontinued
0.7278	Intermediate Similarity	NPD2534	Approved
0.7278	Intermediate Similarity	NPD2533	Approved
0.7278	Intermediate Similarity	NPD2532	Approved
0.7273	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6599	Discontinued
0.7267	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6797	Phase 2
0.7248	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD8312	Approved
0.7225	Intermediate Similarity	NPD8313	Approved
0.7222	Intermediate Similarity	NPD3026	Approved
0.7222	Intermediate Similarity	NPD7411	Suspended
0.7222	Intermediate Similarity	NPD7110	Phase 1
0.7222	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3023	Approved
0.7215	Intermediate Similarity	NPD7390	Discontinued
0.7215	Intermediate Similarity	NPD6799	Approved
0.7212	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3749	Approved
0.7211	Intermediate Similarity	NPD2797	Approved
0.7209	Intermediate Similarity	NPD7251	Discontinued
0.7208	Intermediate Similarity	NPD6100	Approved
0.7208	Intermediate Similarity	NPD5406	Approved
0.7208	Intermediate Similarity	NPD5408	Approved
0.7208	Intermediate Similarity	NPD2796	Approved
0.7208	Intermediate Similarity	NPD5405	Approved
0.7208	Intermediate Similarity	NPD2531	Phase 2
0.7208	Intermediate Similarity	NPD6099	Approved
0.7208	Intermediate Similarity	NPD5404	Approved
0.7203	Intermediate Similarity	NPD3025	Approved
0.7203	Intermediate Similarity	NPD3024	Approved
0.7202	Intermediate Similarity	NPD3926	Phase 2
0.7188	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6801	Discontinued
0.7178	Intermediate Similarity	NPD7577	Discontinued
0.7171	Intermediate Similarity	NPD3657	Discovery
0.7171	Intermediate Similarity	NPD1933	Approved
0.7168	Intermediate Similarity	NPD7808	Phase 3
0.7162	Intermediate Similarity	NPD4624	Approved
0.7161	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6875	Approved
0.716	Intermediate Similarity	NPD6876	Approved
0.7153	Intermediate Similarity	NPD17	Approved
0.7153	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3300	Phase 2
0.7152	Intermediate Similarity	NPD6233	Phase 2
0.7152	Intermediate Similarity	NPD6663	Approved
0.7143	Intermediate Similarity	NPD1241	Discontinued
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3748	Approved
0.7133	Intermediate Similarity	NPD9545	Approved
0.7123	Intermediate Similarity	NPD9269	Phase 2
0.7122	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD5736	Approved
0.7113	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4140	Approved
0.7102	Intermediate Similarity	NPD8434	Phase 2
0.7102	Intermediate Similarity	NPD8150	Discontinued
0.7101	Intermediate Similarity	NPD5242	Approved
0.7099	Intermediate Similarity	NPD2649	Approved
0.7099	Intermediate Similarity	NPD2651	Approved
0.7089	Intermediate Similarity	NPD3887	Approved
0.7086	Intermediate Similarity	NPD5109	Approved
0.7086	Intermediate Similarity	NPD5111	Phase 2
0.7086	Intermediate Similarity	NPD5110	Phase 2
0.7083	Intermediate Similarity	NPD5691	Approved
0.7083	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD2488	Approved
0.7079	Intermediate Similarity	NPD2490	Approved
0.7076	Intermediate Similarity	NPD7177	Discontinued
0.7067	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5735	Approved
0.7055	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2353	Approved
0.7051	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7768	Phase 2
0.7032	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5049	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data